2-羟丙基-β-环糊精R-和s -酮洛芬包合物的光谱研究

IF 3 4区 化学 Q2 CHEMISTRY, ANALYTICAL
Chirality Pub Date : 2025-08-12 DOI:10.1002/chir.70045
Asma Obaid, Nujud Maslamani, Ameerah Theqah, Hind Siddiq, Reem Ghubayra, Ibtisam Mousa, Arniza Khairani Mohd Jamil, Siti Munirah Saharin, Sharifah Mohamad
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引用次数: 0

摘要

酮洛芬又称(RS)-2-(3-苯甲酰苯基)-丙酸,分子式为C16H14O3,属于非甾体类抗炎药。r -酮洛芬具有比S-K更强的镇痛作用,因此,人们对对映体识别的研究越来越感兴趣,这可能通过超分子相互作用,特别是主客体反应来完成。以1:1的摩尔比制备分离的RK和SK与0.01 M的HP-β-CD原液的混合物,得到终浓度为6 × 10−4 M。用乙醇制备酮洛芬对映体原液(1mm)。研究人员将特定体积的酮洛芬与2-羟丙基- β-环糊精(HPβ-CD)结合,然后使用光谱方法研究了s -酮洛芬(SK)和r -酮洛芬(RK)对映体如何与HPβ-CD相互作用形成包合物。采用Benesi-Hildebrand图确定包合物的化学计量比和结合常数;两种对映体均与HP-β-CD形成了1:1的包合物。与SK (799 M−1)相比,RK具有更高的结合常数(1038 M−1)。结果表明,HP-β-CD比SK更倾向于与RK形成包合物。在中性pH下,HP-β-CD存在时,RK和SK之间存在显著差异。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin

Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin

Ketoprofen, also known as (RS)-2-(3-benzoylphenyl)-propionic acid, has the molecular formula C16H14O3 and is classified as a non-steroidal anti-inflammatory medication. R-ketoprofen has stronger analgesic effects than S-K, and as a result, there is a growing interest in enantio-recognition research, which may be accomplished through supramolecular interactions, particularly host-guest reactions. A 1:1 molar ratio was used to produce the combination of separate RK and SK and a 0.01 M stock solution of HP-β-CD to get the final concentration of 6 × 10−4 M. Ethanol was used to make stock solutions of ketoprofen enantiomers (1 mM). Researchers combined a specific volume of ketoprofen with 2-hydroxypropyl-beta-cyclodextrin (HPβ-CD) and then used spectroscopic methods to study how the S-ketoprofen (SK) and R-ketoprofen (RK) enantiomers interact with HPβ-CD to form inclusion complexes in an aqueous solution. The Benesi–Hildebrand plot was used to determine the inclusion complexes' stoichiometry ratio and binding constant; both enantiomers displayed a 1:1 stoichiometry ratio inclusion complex with HP-β-CD. Compared with SK (799 M−1), RK has a higher binding constant (1038 M−1). These results showed that HP-β-CD preferred to form inclusion complexes with RK over SK. At neutral pH, there are significant differences between RK and SK when HP-β-CD is present.

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来源期刊
Chirality
Chirality 医学-分析化学
CiteScore
4.40
自引率
5.00%
发文量
124
审稿时长
1 months
期刊介绍: The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties. Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.
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